(3aS,6Z,10E,11aR)-10-(hydroxymethyl)-6-methyl-3-methylidene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2-one

Details

• Internal ID: 1b2e819b-a130-44a5-b161-e17fd8821562
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Germacranolides and derivatives
• IUPAC Name: (3aS,6Z,10E,11aR)-10-(hydroxymethyl)-6-methyl-3-methylidene-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-2-one
• SMILES (Canonical): CC1=CCCC(=CC2C(CC1)C(=C)C(=O)O2)CO
• SMILES (Isomeric): C/C/1=C/CC/C(=C\[C@@H]2[C@@H](CC1)C(=C)C(=O)O2)/CO
• InChI: InChI=1S/C15H20O3/c1-10-4-3-5-12(9-16)8-14-13(7-6-10)11(2)15(17)18-14/h4,8,13-14,16H,2-3,5-7,9H2,1H3/b10-4-,12-8+/t13-,14+/m0/s1
• InChI Key: QELPHSJDYAPDHF-VURSMFHQSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₃
• Molecular Weight: 248.32 g/mol
• Exact Mass: 248.14124450 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 2.52
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9929	99.29%
Caco-2	+	0.7654	76.54%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6154	61.54%
OATP2B1 inhibitior	-	0.8576	85.76%
OATP1B1 inhibitior	+	0.9299	92.99%
OATP1B3 inhibitior	+	0.9460	94.60%
MATE1 inhibitior	-	0.9012	90.12%
OCT2 inhibitior	-	0.5423	54.23%
BSEP inhibitior	-	0.9002	90.02%
P-glycoprotein inhibitior	-	0.8597	85.97%
P-glycoprotein substrate	-	0.8842	88.42%
CYP3A4 substrate	+	0.5296	52.96%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8440	84.40%
CYP3A4 inhibition	-	0.7239	72.39%
CYP2C9 inhibition	-	0.7812	78.12%
CYP2C19 inhibition	-	0.7047	70.47%
CYP2D6 inhibition	-	0.8855	88.55%
CYP1A2 inhibition	+	0.6163	61.63%
CYP2C8 inhibition	-	0.7190	71.90%
CYP inhibitory promiscuity	-	0.8100	81.00%
UGT catelyzed	-	0.7638	76.38%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6443	64.43%
Eye corrosion	-	0.9554	95.54%
Eye irritation	-	0.6698	66.98%
Skin irritation	-	0.6025	60.25%
Skin corrosion	-	0.9242	92.42%
Ames mutagenesis	-	0.7470	74.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.7566	75.66%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	-	0.5250	52.50%
skin sensitisation	-	0.7197	71.97%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	-	0.5000	50.00%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	-	0.6193	61.93%
Acute Oral Toxicity (c)	III	0.5522	55.22%
Estrogen receptor binding	-	0.8506	85.06%
Androgen receptor binding	-	0.5333	53.33%
Thyroid receptor binding	-	0.6818	68.18%
Glucocorticoid receptor binding	+	0.6587	65.87%
Aromatase binding	-	0.8220	82.20%
PPAR gamma	-	0.6232	62.32%
Honey bee toxicity	-	0.9302	93.02%
Biodegradation	-	0.5250	52.50%
Crustacea aquatic toxicity	-	0.7000	70.00%
Fish aquatic toxicity	+	0.9885	98.85%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.30%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.51%	95.56%
CHEMBL2581	P07339	Cathepsin D	91.95%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.68%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.38%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.10%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.35%	89.00%

Plants that contains it

• Centaurea kurdica
• Onopordum laconicum
• Perymenium featherstonei
• Zaluzania grayana

Cross-Links

• PubChem: 101316742
• LOTUS: LTS0039407
• wikiData: Q104909877